I just got the startup screen about the 'Cinderella' button and followed the instructions. It implies I can have multiple Youtube screens open at the same time in little Windows. However I can only have 1 open at a time. When I go to a second YT video, that second video does not have a Cinderella button.
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No problems here with having two PiP windows. Each video you start has its own PiP button to open its video in a PiP window.
Did you drag the top PiP window to reveal other PiP windows hidden under it ?